👋🏽 I'm Pulkit, co-founder & CEO of Chameleon. AMA (especially about PLG, UX, user onboarding etc.)

Back in 2015, I was working on a consumer mobile app, and after spending months trying to improve retention we stumbled onto some major improvements by tweaking the user onboarding…

Since then we wondered why more teams didn’t focus on this and found that it was a hard problem that was tackled ad-hoc and not regularly iterated. We dug deeper and found that improving UX and running in-product experiments clashed with feature building priorities, and the latter often won for young products.

So we started Chameleon, initially to help product teams create better user onboarding… we’ve evolved to now support multiple use cases:

  • Product-led growth
  • Feature discovery
  • Self-serve learning
  • Continuous feedback

I’m happy to talk about anything and everything related to “Product Success” (reducing friction, increasing engagement, battling churn, improving activation etc.) Lots of great reading on these topics on our blog too.

Chameleon has always been a lean, remote-first team. We raised a seed round from True Ventures but are now profitable and growing. Some other topics I’d be happy to talk about include:

  • Hiring in sprints
  • Enabling an asynchronous culture
  • Managing burn
  • Working with anxiety and stress

I’ll be back on Thursday September 10 at 1 pm UK (10 am EST / 5.30 pm India) time to chat :nerd_face:


Note: This AMA is closed for new questions, but you can check out the existing conversations below.

In this AMA, we had Pulkit Agrawal — co-founder and CEO of Chameleon — share his thoughtful insights on initial product GTM strategy, PLG-market fit, a deep-dive into PLG as a product strategy, and more. Dive in!

AMA Index (Pulkit’s brain pickings) :brain:

(founding insights, opinions, and observations; deftly examined and articulated)

A critical mindset shift: “Over time I’m not ‘running a startup’ but ‘doing work.’ And with ‘doing work’ comes a different perspective”
How Chameleon remains intentional about a healthy, asynchronous culture
Why startups must pick a single acquisition channel to master first and brief notes on changing pricing every six months
The stages of the buyer journey we cannot control and what to do about the ones we do
Running a beta well; “TAKE YOUR TIME”
How product-led growth isn’t an either/or choice
How to make the founder-led-sales-to-first-sales-hire transition
How Chameleon learns; “most product teams are not doing a good job with customer research today. It often gets outsourced to design/UX teams only or happens only when developing a new product.”
An early mistake that cost Chameleon 9 months
Move from: Is a particular product fit for PLG?; To: Is a particular workflow a good/bad PLG candidate?
The gains of moving to the coveted valley

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On growing slowly:

“There are lots of opportunities in the Silicon Valley ecosystem. But one of the obvious downsides is the hype and hyperbole around growth. Of course, growth is a crucial part of the startup journey. But before moving too fast, spend time growing slowly, refining your product, and understanding your customers and market. Once enough customers are raving about us, we’ll be switching to fast growth—and we’re excited to share the lessons that the next phase brings. Until then, we’re taking the slow road.”
Source: Why startups should grow slow before they grow fast

On transitioning from founder-led sales:

“The mentality around product and the mentality around sales is a little different. I do enjoy sales because it’s a chance to talk to real customers and real prospects and understand their pains and help solve their problems. But it’s different to a product because it’s not just about shipping and getting stuff out and being productive all the time. There’s a lot of like step wins or step losses. You’re working on something for a long time and then there’s a decision point and you’re either winning or losing. Whereas with a product, you’re continually delivering and it kind of feels good.

But the reason I’m actually thinking about this is because as a founder I was a product person and an engineer, if I’m going to build sales, if I’m going to build a sales team, I need to know what sales is about and I need to be able to inspire leadership around sales too and be able to be conversant with a sales leader as well as kind of sales reps. So that’s kind of my personal learning in sales is how do we do sales? And sales, I’d always considered a dirty word, it’s like someone is trying to fuse you or someone trying to give me something that I don’t want or con me in some way. And I think part of this is the learning that that’s not what sales is. It’s not what great sales is. Great sales is about solving problems and helping communicate the solutions…”
Source: How do you get users to try software with a learning curve?

On user onboarding:

“The best onboarding is not just an intuitive product…Onboarding is the phase between users first coming into contact with your product and them internalizing the value that is being provided. It is you ‘succinctly communicating how your product will do the job for them’ across all facets of their experience with you. User onboarding is the art and science of first impressions; don’t just rely on looking good. Tell everyone!”
Source: The Best Onboarding is NOT Just an Intuitive Product

On investing early in content:

“It was key to do content. We cared about having organic distribution before we spent any money on ads or anything like that. So I was always against using ads too early. We did use ads for testing things. But we didn’t want that to supersede any of the underlying distribution engines. So content was probably the beginning. And it’s something that’s easy for early teams because founders or the early employees are very passionate; they have expertise and especially in new spaces there’s a lot to teach and educate.”
Source: How Chameleon’s Early Growth Was Powered by Quora, Content and In-Product Experiences

Stay in touch: :sunny:

You can follow Pulkit to stay updated with his discoveries and insights:

  1. Pulkit on Twitter
  2. Pulkit on LinkedIn

Hey Pulkit,

So glad to have you on Relay! :slight_smile:

I’d love to hear how team Chameleon thinks about learning, that is what kinds of systems are in place to make the best of the interplay between 1) customer research, 2) insights gleaned from using your own product, and 3) broader developments in the industry (the ascent of the product-led narrative, for instance).

Also, what advice do you have for a founder on hiring the first sales person. Until what stage should a founder sell and how does one know that they’re ready to hire a sales team and to let go of the day-to-day operations of running sales.


Hey Pulkit,

Thanks for doing this session!

What struck me as particularly interesting about Chameleon’s early days was how you decided to reach out to not just any potential customers but established brands like Amplitude and onboarded them as first users; that, too, without having a functioning product. Would be great to hear the whys behind it, how it helped, and how differently would you approach it today.


Hi Pulkit,

Thanks for taking time to do an AMA. Here at Progression we’ve drunk a full bottle of PLG Kool-aid!

My question for you is this: how would you determine if a particular product is not a good candidate for PLG?

To take two extremes:

  1. a social media image editing tool could be a 100% PLG
  2. an HR system that needs extensive configuration would, I assume, be much harder to facilitate PLG.

Do you have a methodology for how you think about the product and customer and to what extent traditional PLG strategies can be applied?

Bonus question: how is Silicon Valley life for a UK founder in the age of covid? Do you feel like there is a compelling reason for ambitious UK startups to move out there or does it just mean we can Zoom from the same time zone?


Hi Pulkit,

Thanks for spending time with us.

We are an early stage org, we have our core product ready and making progress around other components like User Onboarding, Content, Self care, along with the core product feature backlog etc…

Talking of PLG:
a. Is there a minimul qualifier for PLG direction (Like a product - PLG fit)
b. What in your experience would be the blocks to be addressed in their order of priority for PLG (or) should it all be parallel effort?

Logesh G


Hi Pulkit,

Thanks for doing this AMA with us. I love how you have built a great company and a wonderful product. Congratulations! We are now fully remote and plan to stay that way. It would be great to hear how you engage and motivate your remote teams and what you mean by an asynchronous culture.

Best regards


Hey Pulkit,

Thanks for doing the AMA!

If you were to go back to 2016, during those early months, what did running a successful beta program mean to you? How did you think about measuring progress, both quantitatively and qualitatively? Something you’d revisit and do differently?


Hey Pulkit, Thanks for doing this AMA! :slight_smile:

Here’s my question: Given how all-consuming running a startup can be, how do you manage your anxiety and stress on an every day basis? Also, how has it evolved compared to your early-days of significantly higher uncertainty and involvement.


Hi Pulkit,

For early stage companies it is crucial to pick the right battles. We are in the process of building our sales channels. Which sales channels worked best for you in the early days. For example mass cold emailing, fb ads, capterra ads, content inbound etc.

What kind of pricing worked for you in the early days? Did you give custom quotes or was the pricing published on your website?

Thanks for the AMA!


hey @aditi1002 glad you’re asking about this; too many founders assume that it’s just something that should happen naturally or passively, but it’s not often the case.

In the early days I assumed the startup was a sprint and I had to sink all my energy into it. After a few years I realized that I had a similar state-of-mind, regardless of progress and problems. I felt hurried and assumed at any step the whole thing could come crashing down.

Over time I’m not “running a startup” but “doing work”. And with “doing work” comes a different perspective:

  • Work is not the only thing in my life; I have other key priorities
  • Work is meant to be fulfilling and rewards
  • I should enjoy my work each day and each week and each month

If I was in a job and work took over my life and I was unhappy then I’d quit. So why do I need to create an environment where work isn’t the things above.

Some specific things that have worked for me:

  • Confiding anxieties in a partner or co-founder or mentor. Having someone listen that can re-assure you that things are okay
  • Making physical health a priority; exercising every day / regularly
  • Celebrating all the small wins in a big way

I do meditate and have been for years, and although so many people claim it as a solution to anxiety, I find that the benefits of this to be slow and often invisible. One thing that has been effective is being part of a meditation group where the teacher takes questions and helps provide perspective. The group I’m a part of and you can also join is sundaysangha.org.


hey @raviramani :wave:
initially we decided to have Chameleon distributed but with everyone in the same timezone (Pacific Time). This was because we had heard that managing different timezones was amongst the hardest things to solve for remote teams.

We had folks in Seattle, Portland, SF Bay Area, SoCal and Vancouver. However a couple people on the team wanted to relocate to other places (East Coast, Australia) and we wanted to continue working with them. We also ended up finding someone in Europe that we really liked… so we were almost forced to give up the goal of sticking on the same time zone.

And that means that if anyone gets blocked waiting on input from someone else then it can waste half a day. Therefore we had to be intentional about creating systems that allowed more asynchronous work and avoid the “shoulder tapping” culture that can exist in offices.

Some specific ways that we establish this:

  • Clear Google Drive structure so anyone can find documents they might need
  • Providing updates on tasks within Trello so anyone can see status and progress
  • Clear assignment rules for who is responsible/owns what, so it’s clear when tasks are thrown over to the next person
  • Clear that Slack is not the place to manage or assign tasks – that happens in Trello; while Slack is for conversation. Ideally discussion about a specific task happens in its Trello card
  • Giving clear guidelines around expectations for availability on Slack; we shouldn’t assume the other person will reply immediately, even when tagged, so plan accordingly
  • Making sure there are multiple threads of work so that if one is waiting, you can continue with other items
  • Recording external calls with Zoom (and recently, transcribing with Grain) and making those shared so that folks can access key content

From my experience the most important aspect of a healthy remote culture is trust. You have to trust that people on your teams want to do their best work. Your goal is to encourage, enable, and empower them. Avoid micro-managing or doubting effort.

Would love to know what you’ve learnt in your process of going remote! Any insights to share?


Hey Pulkit,

Great to see you here.

A couple of questions:
Content as a channel - love the content on your blog. But as a company, we have often struggled to convert content traffic to signups/ leads. Can you share your experiences around this.

Love the idea of growing slow to grow fast. What do you think are the indicators - that should trigger the switch to fast growth mode.


@kush in many ways we are still figuring this out and I expect most companies have to keep figuring this out as they grow and the market evolves.

My biggest lesson = keep it simpleSimpler than you think is simple. Leave money on the table; it’s okay not to optimize at this stage.

I’d suggest you pick ONE channel (e.g. cold emails / content + inbound / partnerships) because it’ll take 6+ months for it to start working well. Pick the channel that’s already kind of working or based on the type of buyer* you have.

  • If your buyers will take cold calls and their phone numbers are available then you can do cold outbound… if your buyers read a lot of online content and you feel like you can differentiate then do that. Generally I think the more scalable channels (marketing-led or product-led) are the ones of the future (vs. sales-led) but it also depends on your product complexity and the need for customization/personalization in the sales process.

RE: Pricing – we experimented quite a lot in the early days. We changed prices every 6 months. Generally this went upwards (it’s a little harder to go the other way I think.)

If you are running a sales-led process then you can provide custom quotes. If you are doing self-serve then you’ll probably need to publish. We find that even if we provide custom quotes, buyers do want to have a sense of the possible cost early, so you’ll probably still need some simple framework for pricing even if you don’t publish it.

Does that answer your questions sufficiently? Let me know if you’d like me to expand or if you have more specific questions


hi @Vengat, with the caveat that we’re still making this better, the main approach we’re taking is:

  1. Content gets people to the site
  2. Find a way to get their email address
  3. Nurture them on email
  4. Leverage webinars or other free tools to drive forward engagement
  5. Be ready to engage when they’re ready to evaluate

Underpinning this is the understanding of the buyer journey:

Unaware > Aware > Considering > Evaluating > Decision

In these stages, the one we don’t control is Considering > Evaluating: this has a lot of factors that are to do with the buyer being ready (e.g. internal team alignment, business priorities etc.)

So we should focus on the other stages… if your market is established then you don’t need to worry about unaware > aware (or you can let the big players do this job) so you can focus on aware > considering. Here your goal with content is to help your potential buyers visualize how your product can meet their needs; give them ideas and inspire them. Then when they’re ready they’ll actually begin evaluating.

Does that give you a framework to try some stuff? Why do you think your traffic isn’t converting?


I think this will come naturally when you’ve really hit PM Fit. At that point you’ll get way more demand than you can handle, and you’ll need to lean-in to that by hiring more. It’s hard to generalize but Peter Reinhardt gave a good talk on finding PM Fit so check that out.


Good question @Akhilesh. I think the best version of this I’ve seen is how Superhuman handled it. Have you read the article on First Round Review?

I would recommend making any beta about finding PM Fit. It might be for a feature or for your product. I think one mistake we made was assuming we didn’t have time and rushing this. TAKE YOUR TIME. If you rush now, it will cost you more time later. Keep iterating and keep working with early customers until they are fans and are raving about the product.

One thing we’ve been helping customers with recently is building in “continuous feedback” into their products. We spend so much time on quantitative analysis that we’ve really neglected getting high quality qualitative feedback from users to learn why, and to hear in their own words what they expect. I wrote more about how and why we need a new model for user feedback in the age of product-led.


yes! :slight_smile:

it depends on how self-serve the product is and how savvy the buyer is. For example, a social media management tool (like Buffer) must leverage PLG because buyers expect a self-serve approach; it’s relatively simple to understand; the price-point is low etc.

If your product is high-complexity, needs implementation support, is new (with limited expertise from buyers), needs a lot of cross-team alignment to purchase, has a high learning curve etc. then it likely will need more of a human touch.

However it doesn’t need to be either PLG or not-PLG; there can be a balance. A human-assisted PLG approach can be very effective – combining prompts inside the product with access to people to answer questions and provide guidance.

Does that answer your question @Logesh?


Very timely question because we just wrote a detailed guide on how to find and address blocks for PLG!

Check it out and let me know if you have any questions @Logesh!

We’re also running a webinar and workshop on the topic of how to discover and unlock bottlenecks to product-led growth, so sign-up from the blog post above.


hey @Krish I’d be interested in your perspective on this question too! How did you do it?

I think a founder can let go of day-to-day operations of running sales once you’ve hired a sales leader (or VP). But from my perspective that happens after you have a small functioning sales team (e.g. 2 AEs and 2 SDRs). My perspective on running a company is to do all the leadership roles before hiring someone to replace you, rather than hiring a leader early and outsourcing the building of a team to them.

I think as you hire sales people, the role of a founder doing sales changes. In the beginning I was doing all the pipeline development, demos, closing etc. Now the pipeline/demand-gen is handled mostly by marketing and our sales team does qualification, demos, closing etc. My role is to be a product expert and offer best practices and build confidence in the buyer that we will solve their problems. I try to join all sales calls where the prospect might benefit from some coaching or wherever there are executives on the call. I also try to establish a one-to-one / direct line of communication (via email) with the budget holder or contract signatory, even while the sales team is running its process.